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Abstract:

The present invention relates to a photosensitive composition including
an acrylate-based compound having an adamantyl structure. It is possible
to manufacture an organic thin film that is easily stripped without
decreasing the strength of the thin film by using the photosensitive
composition.

Claims:

1. A photosensitive composition comprising: a binder resin including an
alkali soluble polymer resin; a crosslinking compound; a
photopolymerization initiator; an acrylate-based compound represented by
the following Formula 1; and a solvent: ##STR00006## wherein at least
one of R1 to R4 is represented by the following Formula 2,
Formula 3, Formula 4, or Formula 5, and the rest are selected from the
group consisting of hydrogen, a halogen group, an alkyl group having 1 to
5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, and a
haloalkyl group having 1 to 5 carbon atoms, ##STR00007## wherein
R5, R6, R7 and R8 are the same as or different from
each other, and each independently hydrogen, or an alkyl group having 1
to 5 carbon atoms.

2. The photosensitive composition according to claim 1, wherein R1
and R2 of Formula 1 are each independently represented by Formula 2,
Formula 3, Formula 4 or Formula 5, and R3 and R4 are hydrogen.

3. The photosensitive composition according to claim 1, wherein Formula 1
is represented by any one of the following Formula 6 to Formula 13:
##STR00008## ##STR00009## ##STR00010##

4. The photosensitive composition according to claim 1, wherein a content
of the acrylate-based compound is 0.8 to 4 wt % on the basis of a total
weight of the photosensitive composition.

5. The photosensitive composition according to claim 1, wherein a content
of the acrylate-based compound is 5 to 25 wt % on the basis of a weight
of the crosslinking compound.

6. The photosensitive composition according to claim 1, wherein the
binder resin is an acryl-based binder resin including a carboxyl group.

7. The photosensitive composition according to claim 1, wherein a content
of the binder resin is 1 to 20 wt % on the basis of a total weight of the
photosensitive composition.

8. The photosensitive composition according to claim 1, wherein a content
of the crosslinking compound is 1 to 30 wt % on the basis of a total
weight of the photosensitive composition.

9. The photosensitive composition according to claim 1, wherein a content
of the photopolymerization initiator is 0.1 to 5 wt % on the basis of a
total weight of the photosensitive composition.

10. The photosensitive composition according to claim 1, wherein a
content of the solvent is 45 to 95 wt % on the basis of a total weight of
the photosensitive composition.

11. The photosensitive composition according to claim 1, wherein in the
case where a thin film is formed by applying the photosensitive
composition to a board, the strength of the thin film is 0.24 GPa or
more.

12. The photosensitive composition according to claim 1, further
comprising: one or more selected from the group consisting of a colorant,
a curing accelerator, a thermal polymerization inhibitor, a surfactant, a
photosensitizer, a plasticizer, an adhesion promoter, a filler and an
adhesive preparation.

13. The photosensitive composition according to claim 1, wherein the
photosensitive composition is selected from the group consisting of a
photosensitive composition for photoacryl, a photosensitive composition
for a touch panel protection material, a photosensitive composition for a
color filter, a black matrix photosensitive composition, a photosensitive
composition for an overcoat layer, a photosensitive composition for a
column spacer, a photosensitive composition for a photocurable paint, a
photosensitive composition for photocurable ink, a photosensitive
composition for a photocurable adhesive agent, a photosensitive
composition for a printed board, and a photosensitive composition for a
printed circuit board.

14. A composition for improving a developing property, comprising: the
acrylate-based compound represented by Formula 1 of claim 1.

15. A sensitive material, comprising: the photosensitive composition
according to claim 1.

16. The sensitive material according to claim 15, wherein the sensitive
material is selected from the group consisting of a sensitive material
for photoacryl, a sensitive material for a touch panel protection
material, a pigment dispersion type sensitive material for manufacturing
a color filter, a sensitive material for forming a black matrix, a
sensitive material for forming an overcoat layer, a column spacer
sensitive material, and a sensitive material for a printed circuit board.

17. A sensitive material, comprising: the photosensitive composition
according to claim 2.

18. A sensitive material, comprising: the photosensitive composition
according to claim 3.

Description:

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims priority to and the benefit of Korean
Patent Application No. 10-2010-0115557 filed in the Korean Intellectual
Property Office on Nov. 19, 2010, the entire contents of which are
incorporated herein by reference.

TECHNICAL FIELD

[0002] The present invention relates to a photosensitive composition
including an acrylate-based compound that can increase a developing
property of a photosensitive composition.

BACKGROUND ART

[0003] In manufacturing a color filter of a liquid crystal display diode,
a photosensitive composition is used as an essential material. For
example, a color pixel exhibiting a color, a black matrix for blocking
light, an overcoat for compensating a step between pixels, and a column
spacer maintaining a cell-gap of a liquid crystal display diode are all
constituted by a thin film layer that is formed of a photosensitive
composition by a photolithography process and has a thickness of 5 μm
or less. In addition, since the photosensitive composition that is used
for a column spacer or an overcoat can also be used for passivation of a
thin film transistor layer, a characteristic of the photosensitive
composition largely affects productivity and quality of a color filter
and a liquid crystal display diode.

[0004] After the color filter is manufactured or after a passivation
process of the thin film transistor, defects may occur. This may be
caused by adhesion of foreign materials floating in the air, or by a
minute damage in a thin film layer during storage or in a progress of
process. In this case, in the case where defective portions are fine, the
portions may be locally treated by applying a repair process, but in the
case where the treatment is impossible, a glass substrate having a
relatively high cost is regenerated by reworking the color filter or thin
film transistor substrate. Since chemicals used in the reworking are
mostly toxic, glass should be regenerated at a temperature that is as low
as possible or for a short treatment period of time.

[0005] However, if the thin film is formed softly in order to
advantageously perform the reworking, there may be problems in that the
thin film is easily damaged or afterimages are formed when the liquid
crystal display diode is driven. Accordingly, there is a need to develop
a composition that can manufacture a thin film that is easily reworked
while strength of the thin film is maintained.

SUMMARY OF THE INVENTION

[0006] The present invention has been made in an effort to provide a
photosensitive composition including an acrylate-based compound that can
manufacture a thin film that is easily stripped without decreasing
strength.

[0007] An exemplary embodiment of the present invention provides a
photosensitive composition, including: a binder resin including an alkali
soluble polymer resin; a crosslinking compound; a photopolymerization
initiator; an acrylate-based compound represented by the following
Formula 1; and a solvent.

##STR00001##

[0008] wherein

[0009] at least one of R1 to R4 is represented by the following
Formula 2, Formula 3, Formula 4, or Formula 5, and

[0010] the rest are selected from the group consisting of hydrogen, a
halogen group, an alkyl group having 1 to 5 carbon atoms, an alkoxy group
having 1 to 5 carbon atoms, and a haloalkyl group having 1 to 5 carbon
atoms,

##STR00002##

[0011] wherein

[0012] R5, R6, R7 and R8 are the same as or different
from each other, and each independently hydrogen, or an alkyl group
having 1 to 5 carbon atoms.

[0013] Another exemplary embodiment of the present invention provides a
composition for improving a developing property, including: the
acrylate-based compound represented by Formula 1.

[0015] According to the exemplary embodiment of the present invention, an
acrylate-based compound may be more usefully applied to a photosensitive
composition by including at least one acrylate group with an adamantyl
structure as the center. The photosensitive composition according to the
exemplary embodiment of the present invention may shorten the developing
time in a photolithography process without decreasing strength of a thin
film.

BRIEF DESCRIPTION OF THE DRAWINGS

[0016] FIG. 1 illustrates results of observing whether a pattern is formed
or not by a scanning electron microscope after developing is performed by
using a composition of Example 1.

[0017] FIG. 2 illustrates results of observing whether a pattern is formed
or not by a scanning electron microscope after developing is performed by
using a composition of Comparative Example 2, in which a width
represented by an arrow is 5.20 μm.

DETAILED DESCRIPTION

[0018] Hereinafter, the present invention will be described in detail.

[0019] The photosensitive composition according to the exemplary
embodiment of the present invention includes a binder resin including an
alkali soluble polymer resin, a crosslinking compound including two or
more unsaturated acryl groups, a photopolymerization initiator, an
acrylate-based compound represented by Formula 1, and a solvent.

[0020] The acrylate-based compound represented by Formula 1 includes at
least one acrylate group with an adamantyl structure as the center.

[0021] In the acrylate-based compound according to the exemplary
embodiment of the present invention, substituent groups of Formula 1 will
be described in more detail below. As the halogen group, there may be
--F, --Cl, --Br, and --I, but the group is not limited thereto.

[0022] The alkyl group may be a straight or branched chain, and the number
of carbon atoms is not particularly limited but is preferably 1 to 5. As
specific examples thereof, there are a methyl group, an ethyl group, a
propyl group, an isopropyl group, a butyl group, and a t-butyl group, but
the examples are not limited thereto.

[0023] The alkoxy group may have 1 to 5 carbon atoms, and specifically,
there may be methoxy, ethoxy, and isopropyloxy, but the group is not
limited thereto.

[0024] The haloalkyl group may have 1 to 5 carbon atoms, and means a
functional group in which one or more hydrogens of the alkyl group are
substituted by the halogen group.

[0025] In addition, the composition for improving a developing property
according to the exemplary embodiment of the present invention includes
the acrylate-based compound represented by Formula 1.

[0026] The composition for improving a developing property may be a
photosensitive composition as described above.

[0027] In Formula 1, R1 and R2 are each independently
represented by Formula 2, Formula 3, Formula 4, or Formula 5, and R3
and R4 may be hydrogen, but are not limited thereto.

[0028] In the acrylate-based compound according to the exemplary
embodiment of the present invention, specifically, Formula 1 may be
represented by any one of the following Formula 6 to Formula 13.

##STR00003## ##STR00004## ##STR00005##

[0029] Since the central structure of the molecule of the acrylate-based
compound according to the exemplary embodiment of the present invention
has a bulky multicyclic shape, when a neutralization reaction is
progressed by mixing the polymer thin film and the alkali developing
solution and the thin film is dissolved, the molecules in the thin film
are allowed to be more easily separated from each other.

[0030] According to the exemplary embodiment of the present invention, the
acrylate-based compound may be more usefully applied to the
photosensitive composition by including at least one acrylate group with
the adamantyl structure as the center. The photosensitive composition
according to the exemplary embodiment of the present invention may
shorten the developing time in a photolithography process without
decreasing the strength of the thin film.

[0031] In the photosensitive composition according to the exemplary
embodiment of the present invention, the content of the acrylate-based
compound represented by Formula 1 is preferably 0.8 to 4 wt % on the
basis of the total weight of the photosensitive composition. In the case
where the content of the acrylate-based compound represented by Formula 1
is 0.8 wt % or more on the basis of the total weight of the
photosensitive composition, an improving effect in stripping is good, and
in the case where the content is 4 wt % or less, there is an effect of
preventing a decrease in strength of the thin film.

[0032] In the photosensitive composition according to the exemplary
embodiment of the present invention, the content of the acrylate-based
compound represented by Formula 1 is preferably 5 to 25 wt %, and
specifially 5 to 20 wt % on the basis of the weight of the crosslinking
compound. In the case where the content of the acrylate-based compound
represented by Formula 1 is 5 wt % or more on the basis of the weight of
the crosslinking compound, an improving effect in stripping is good, and
in the case where the content is 25 wt % or less, there is an effect of
preventing a decrease in strength of the thin film.

[0033] Since the photosensitive composition according to the exemplary
embodiment of the present invention includes the binder resin, there is
an effect of controlling viscosity and there is an effect of making
patterning using an alkali developing solution possible.

[0034] As the binder resin, matters such as an alkali soluble binder
resin, which are generally used in the art may be used. Specifically, an
acryl-based binder resin including a carboxyl group may be used, and more
specifically, a matter that is configured by copolymerizing a monomer
providing mechanical strength of the film and a monomer providing alkali
solubility may be used.

[0036] As the monomer providing alkali solubility, for example, one or
more selected from the group consisting of (metha)acrylic acid, crotonic
acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid,
5-nobonen-2-carboxylic acid, mono-2-((metha)acryloyloxy)ethyl phthalate,
mono-2-((metha)acryloyloxy)ethyl succinate, and
co-carboxypolycaprolactone mono(metha)acrylate are preferably used, but
the monomer is not limited thereto.

[0037] In addition, for the binder resin, specifically, a weight average
molecular weight may be 3,000 to 150,000. If the molecular weight is
3,000 or more, there is an effect of preventing the pattern from being
lost during the developing process, and if the molecular weight is less
than 150,000, there is an effect of preventing a problem that it is
difficult to perform coating because viscosity is increased.

[0038] The content of the binder resin may be 1 to 20 wt % on the basis of
the total weight of the photosensitive composition, but is not limited
thereto. If the content of the binder resin is 1 wt % or more, there is
an effect in which pattern can be performed by using the alkali aqueous
solution, if the content is less than 20 wt %, there is an effect of
preventing the pattern from being lost during the developing process.

[0039] In the photosensitive composition according to the exemplary
embodiment of the present invention, as the crosslinking compound,
specifically, a crosslinking compound including an ethylene-based
unsaturated group may be used, more specifically, a crosslinking compound
including two or more unsaturated acryl groups, and a crosslinking
compound including three or more unsaturated acryl groups may be used.
Specific examples thereof may include one or more selected from the group
consisting of a compound that is obtained by esterifying polyvalent
alcohol such as ethyleneglycol di(metha)acrylate, polyethylene glycol
di(metha)acrylate in which the number of ethylene groups is 2 to 14,
trimethylolpropane di(metha)acrylate, trimethylolpropane
tri(metha)acrylate, pentaerythritol tri(metha)acrylate, pentaerythritol
tetra(metha)acrylate, 2-trisacryloyloxymethylethyl phthalate, propylene
glycol di(metha)acrylate in which the number of propylene groups is 2 to
14, dipentaerythritol penta(metha)acrylate, dipentaerythritol
hexa(metha)acrylate, and a mixture of an acidic denatured material of
dipentaerythritol penta(metha)acrylate and dipentaerythritol
hexa(metha)acrylate (trademark: TO-2348, and TO-2349 manufactured by
Toagosei Co., Ltd. in Japan) by a α,β-unsaturated carboxylic
acid; a compound that is obtained by adding a (metha)acrylic acid to a
compound including a glycidyl group such as an addition product of
trimethylolpropane triglycidyletheracrylic acid and an addition product
of bisphenol A diglycidyletheracrylic acid; an addition product of a
hydroxyl group such as diester phthalate of
β-hydroxyethyl(metha)acrylate and an addition product of toluene
diisocyanate of β-hydroxyethyl (metha)acrylate, or an addition
product of a compound having an ethylene unsaturated bond and an ester
compound with polyvalent carboxylic acid or polyisocyanate;
(metha)acrylate alkylester such as methyl(metha)acrylate,
ethyl(metha)acrylate, butyl(metha)acrylate, and
2-ethylhexyl(metha)acrylate; and
9,9'-bis[4-(2-acryloyloxyethoxy)phenyl]fluorine, but are not limited
thereto, and general matters that are known in the art may be used. In
some cases, silica dispersion element may be used in these compounds, for
example, there are Nanocryl XP series (0596, 1045, 21/1364) and Nanopox
XP series (0516, 0525) manufactured by Hanse Chemie Co., Ltd.

[0040] The content of the crosslinking compound may be 1 to 30 wt % on the
basis of the total weight of the photosensitive composition, but is not
limited thereto.

[0041] In the photosensitive composition according to the exemplary
embodiment of the present invention, as the photopolymerization
initiator, for example, a triazine-based compound such as
2,4-trichloromethyl-(4'-methoxyphenyl)-6-triazine,
2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine,
2,4-trichloromethyl-(fipronil)-6-triazine,
2,4-trichloromethyl-(3',4'-dimethoxyphenyl)-6-triazine,
3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propanoic acid,
2,4-trichloromethyl-(4'-ethylbiphenyl)-6-triazine, and
2,4-trichloromethyl-(4'-methylbiphenyl)-6-triazine; a biimidazole
compound such as 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl
biimidazole, and
2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole; an
acetophenone-based compound such as
2-hydroxy-2-methyl-1-phenylpropane-1-one,
1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1-one,
4-(2-hydroxyethoxy)-phenyl (2-hydroxy)propyl ketone, 1-hydroxycyclohexyl
phenyl ketone, 2,2-dimethoxy-2-phenyl acetophenone,
2-methyl-(4-methylthiophenyl)-2-morpholino-1-propane-1-one(Irgacure-907),
and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butane-1-one(Irgacure-
-369); an O-acyloxime-based compound such as Irgacure OXE 01 and Irgacure
OXE 02 manufactured by Ciba Geigy Co., Ltd.; a benzophenone-based
compound such as 4,4'-bis(dimethylamino)benzophenone, and
4,4'-bis(diethylamino)benzophenone; a thioxantone-based compound such as
2,4-diethyl thioxantone, 2-chloro thioxantone, isopropyl thioxantone,
diisopropyl thioxantone; a phosphine oxide-based compound such as
2,4,6-trimethylbenzoyl diphenylphosphine oxide,
bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide, and
bis(2,6-dichlorobenzoyl) propyl phosphine oxide; and a coumarine-based
compound such as 3,3'-carbonylvinyl-7-(diethylamino)coumarine,
3-(2-benzothiazolyl)-7-(diethylamino)coumarine,
3-benzoyl-7-(diethylamino)coumarine, 3-benzoyl-7-methoxy-coumarine, and
10,10'-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H--Cl]--
benzopyrano[6,7,8-ij]-quinolizine-11-one may be used alone or in a mixture
of two or more.

[0042] The content of the photopolymerization initiator may be 0.1 to 5 wt
% on the basis of the total weight of the photosensitive composition, but
is not limited thereto.

[0044] The content of the solvent may be 45 to 95 wt % on the basis of the
total weight of the photosensitive composition, but is not limited
thereto.

[0045] In addition, the photosensitive composition according to the
exemplary embodiment of the present invention may further include one or
more selected from the group consisting of a colorant, a curing
accelerator, a thermal polymerization inhibitor, a surfactant, a
photosensitizer, a plasticizer, an adhesion promoter, a filler, and an
adhesive preparation according to the purpose.

[0047] The curing accelerator, for example, may include one or more
selected from the group consisting of 2-mercaptobenzoimidazole,
2-mercaptobenzothiazole, 2-mercaptobenzoxazole,
2,5-dimercapto-1,3,4-thiadiazole, 2 mercapto-4,6-dimethylaminopyrydine,
pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol
tris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate),
pentaerythritol tris(2-mercaptoacetate), trimethylolpropane
tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate),
trimethylolethane tris(2-mercaptoacetate), and trimethylolethane
tris(3-mercaptopropionate), but is not limited thereto, and may include
matters that are generally known in the art.

[0048] The thermal polymerization inhibitor, for example, may include one
or more selected from the group consisting of p-anisole, hydroquinone,
pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium
salt, N-nitrosophenylhydroxyamine aluminum salt, and phenothiazine, but
is not limited thereto, and may include matters that are generally known
in the art.

[0049] As the surfactant, photosensitizer, plasticizer, adhesion promoter,
and filler, all compounds that can be included in a known photosensitive
resin composition may be used.

[0050] The content of the colorant is preferably 1 to 20 wt % on the basis
of the total weight of the photosensitive composition, and the contents
of the other additives are each independently preferably 0.01 to 5 weight
on the basis of the total weight of the photosensitive composition, but
are not limited thereto.

[0051] Meanwhile, a transparent photosensitive composition according to
the exemplary embodiment of the present invention is used in a roll
coater, a curtain coater, a spin coater, a slot die coater, and various
printings and precipitations, and may be applied on a support of metal,
paper, glass, and plastic substrates. In addition, the composition may be
transferred on the other support after being coated on the support such
as a film, or may be transferred on a blanket after being coated on a
first support and transferred on a second support again, but the
application method thereof is not particularly limited.

[0052] As a light source for curing the transparent photosensitive
composition of the present invention, for example, there are a mercury
vapor arc, a carbon arc, and a Xe arc emitting light having a wavelength
of 250 to 450 nm, but the light source is not limited thereto.

[0053] In the case where the photosensitive composition of the exemplary
embodiment of the present invention forms a thin film by being applied to
a board, strength of the thin film is 0.21 GPa or more, and specifically,
0.24 GPa or more. If the strength of the thin film is 0.21 GPa or more,
an effect of the thin film may be obtained, and if the strength is 0.24
GPa or more, the thin film is more excellent. Accordingly, when the thin
film is formed by the photosensitive composition according to the
exemplary embodiment of the present invention, there is an effect that
stripping is easily performed without decreasing the strength of the thin
film. The board includes, for example, a support such as metal, paper,
glass, and plastic substrates, but is not limited thereto.

[0054] The photosensitive composition according to the exemplary
embodiment of the present invention may be selected from the group
consisting of a photosensitive composition for photoacryl, a
photosensitive composition for a touch panel protection material, a
photosensitive composition for a TFT LCD color filter, a black matrix
photosensitive composition of a TFT LCD or organic light emitting diode,
a photosensitive composition for an overcoat layer, a photosensitive
composition for a column spacer, a photosensitive composition for a
photocurable paint, a photosensitive composition for photocurable ink, a
photosensitive composition for a photocurable adhesive agent, a
photosensitive composition for a printed board, and a photosensitive
composition for a printed circuit board, but is not limited thereto.

[0055] The photosensitive composition according to the exemplary
embodiment of the present invention may be used as a sensitive material
selected from the group consisting of a sensitive material for
photoacryl, a sensitive material for a touch panel protection material, a
pigment dispersion type sensitive material for manufacturing a TFT LCD
color filter, a sensitive material for forming a black matrix of a TFT
LCD or organic light emitting diode (OLED), a sensitive material for
forming an overcoat layer of an LCD or OLED, a column spacer sensitive
material, a sensitive material for a printed board or printed circuit
board, and a transparent sensitive material. In addition, the composition
may be used in manufacturing PDP, and as partition materials for OLED and
LED lighting, but the purpose thereof is not particularly limited.

[0056] Hereinafter, preferable Examples, Comparative Examples, and Test
examples will be described in order to help understand the present
invention. However, the following Examples, Comparative Examples, and
Test examples are set forth to illustrate the present invention, but the
scope of the present invention is not limited thereto.

EXAMPLE

Example 1

[0057] The following photosensitive compositions were manufactured in
order to confirm the effect of the exemplary embodiment of the present
invention. 8 parts by weight of the binder BzMA/MAA (molar ratio: 70/30,
Mw: 24,000) formed of the alkali soluble resin, 16 parts by weight of the
dipentaerythritol hexaacrylate compound as the crosslinking compound, 1
part by weight of Irgacure 369
(2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butane-1-one)
manufactured by Ciba-Geigy Co., Ltd. as the photopolymerization
initiator, 0.8 parts by weight (5% of the crosslinking compound) of the
acrylate-based compound represented by Formula 6, and PGMEA which was the
organic solvent were put so that the total content was 100 parts by
weight, and mixed by using the shaker for 3 hours to form the solution,
and the solution was filtered with the filter of 5 microns.

Example 2

[0058] The same manner as Example 1 was performed, except that 1.6 parts
by weight (10% of the crosslinking compound) of the acrylate-based
compound was used instead of 0.8 parts by weight (5% of the crosslinking
compound) of the acrylate-based compound represented by Formula 6 in
Example 1.

Example 3

[0059] The same manner as Example 1 was performed, except that 2.4 parts
by weight (15% of the crosslinking compound) of the acrylate-based
compound was used instead of 0.8 parts by weight (5% of the crosslinking
compound) of the acrylate-based compound represented by Formula 6 in
Example 1.

Example 4

[0060] The same manner as Example 1 was performed, except that 3.2 parts
by weight (20% of the crosslinking compound) of the acrylate-based
compound was used instead of 0.8 parts by weight (5% of the crosslinking
compound) of the acrylate-based compound represented by Formula 6 in
Example 1.

Example 5

[0061] The same manner as Example 1 was performed, except that 4.0 parts
by weight (25% of the crosslinking compound) of the acrylate-based
compound was used instead of 0.8 parts by weight (5% of the crosslinking
compound) of the acrylate-based compound represented by Formula 6 in
Example 1.

Example 6

[0062] The same manner as Example 1 was performed, except that 0.8 parts
by weight (5% of the crosslinking compound) of the acrylate-based
compound represented by Formula 7 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 7

[0063] The same manner as Example 1 was performed, except that 1.6 parts
by weight (10% of the crosslinking compound) of the acrylate-based
compound represented by Formula 7 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 8

[0064] The same manner as Example 1 was performed, except that 2.4 parts
by weight (15% of the crosslinking compound) of the acrylate-based
compound represented by Formula 7 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 9

[0065] The same manner as Example 1 was performed, except that 3.2 parts
by weight (20% of the crosslinking compound) of the acrylate-based
compound represented by Formula 7 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 10

[0066] The same manner as Example 1 was performed, except that 4.0 parts
by weight (25% of the crosslinking compound) of the acrylate-based
compound represented by Formula 7 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 11

[0067] The same manner as Example 1 was performed, except that 0.8 parts
by weight (5% of the crosslinking compound) of the acrylate-based
compound represented by Formula 8 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 12

[0068] The same manner as Example 1 was performed, except that 1.6 parts
by weight (10% of the crosslinking compound) of the acrylate-based
compound represented by Formula 8 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 13

[0069] The same manner as Example 1 was performed, except that 2.4 parts
by weight (15% of the crosslinking compound) of the acrylate-based
compound represented by Formula 8 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 14

[0070] The same manner as Example 1 was performed, except that 3.2 parts
by weight (20% of the crosslinking compound) of the acrylate-based
compound represented by Formula 8 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 15

[0071] The same manner as Example 1 was performed, except that 4.0 parts
by weight (25% of the crosslinking compound) of the acrylate-based
compound represented by Formula 8 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 16

[0072] The same manner as Example 1 was performed, except that 0.8 parts
by weight (5% of the crosslinking compound) of the acrylate-based
compound represented by Formula 9 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 17

[0073] The same manner as Example 1 was performed, except that 1.6 parts
by weight (10% of the crosslinking compound) of the acrylate-based
compound represented by Formula 9 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 18

[0074] The same manner as Example 1 was performed, except that 2.4 parts
by weight (15% of the crosslinking compound) of the acrylate-based
compound represented by Formula 9 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 19

[0075] The same manner as Example 1 was performed, except that 3.2 parts
by weight (20% of the crosslinking compound) of the acrylate-based
compound represented by Formula 9 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 20

[0076] The same manner as Example 1 was performed, except that 4.0 parts
by weight (25% of the crosslinking compound) of the acrylate-based
compound represented by Formula 9 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 21

[0077] The same manner as Example 1 was performed, except that 0.8 parts
by weight (5% of the crosslinking compound) of the acrylate-based
compound represented by Formula 10 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 22

[0078] The same manner as Example 1 was performed, except that 1.6 parts
by weight (10% of the crosslinking compound) of the acrylate-based
compound represented by Formula 10 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 23

[0079] The same manner as Example 1 was performed, except that 2.4 parts
by weight (15% of the crosslinking compound) of the acrylate-based
compound represented by Formula 10 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 24

[0080] The same manner as Example 1 was performed, except that 3.2 parts
by weight (20% of the crosslinking compound) of the acrylate-based
compound represented by Formula 10 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 25

[0081] The same manner as Example 1 was performed, except that 4.0 parts
by weight (25% of the crosslinking compound) of the acrylate-based
compound represented by Formula 10 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 26

[0082] The same manner as Example 1 was performed, except that 0.8 parts
by weight (5% of the crosslinking compound) of the acrylate-based
compound represented by Formula 11 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 27

[0083] The same manner as Example 1 was performed, except that 1.6 parts
by weight (10% of the crosslinking compound) of the acrylate compound
represented by Formula 11 was used instead of 0.8 parts by weight (5% of
the crosslinking compound) of the acrylate-based compound represented by
Formula 6 in Example 1.

Example 28

[0084] The same manner as Example 1 was performed, except that 2.4 parts
by weight (15% of the crosslinking compound) of the acrylate-based
compound represented by Formula 11 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 29

[0085] The same manner as Example 1 was performed, except that 3.2 parts
by weight (20% of the crosslinking compound) of the acrylate-based
compound represented by Formula 11 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 30

[0086] The same manner as Example 1 was performed, except that 4.0 parts
by weight (25% of the crosslinking compound) of the acrylate-based
compound represented by Formula 11 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 31

[0087] The same manner as Example 1 was performed, except that 0.8 parts
by weight (5% of the crosslinking compound) of the acrylate-based
compound represented by Formula 12 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 32

[0088] The same manner as Example 1 was performed, except that 1.6 parts
by weight (10% of the crosslinking compound) of the acrylate-based
compound represented by Formula 12 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 33

[0089] The same manner as Example 1 was performed, except that 2.4 parts
by weight (15% of the crosslinking compound) of the acrylate-based
compound represented by Formula 12 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 34

[0090] The same manner as Example 1 was performed, except that 3.2 parts
by weight (20% of the crosslinking compound) of the acrylate-based
compound represented by Formula 12 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 35

[0091] The same manner as Example 1 was performed, except that 4.0 parts
by weight (25% of the crosslinking compound) of the acrylate-based
compound represented by Formula 12 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 36

[0092] The same manner as Example 1 was performed, except that 0.8 parts
by weight (5% of the crosslinking compound) of the acrylate-based
compound represented by Formula 13 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 37

[0093] The same manner as Example 1 was performed, except that 1.6 parts
by weight (10% of the crosslinking compound) of the acrylate-based
compound represented by Formula 13 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 38

[0094] The same manner as Example 1 was performed, except that 2.4 parts
by weight (15% of the crosslinking compound) of the acrylate-based
compound represented by Formula 13 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 39

[0095] The same manner as Example 1 was performed, except that 3.2 parts
by weight (20% of the crosslinking compound) of the acrylate-based
compound represented by Formula 13 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 40

[0096] The same manner as Example 1 was performed, except that 4.0 parts
by weight (25% of the crosslinking compound) of the acrylate-based
compound represented by Formula 13 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 41

[0097] The same manner as Example 1 was performed, except that 0.5 parts
by weight (3% of the crosslinking compound) of the acrylate-based
compound was used instead of 0.8 parts by weight (5% of the crosslinking
compound) of the acrylate-based compound represented by Formula 6 in
Example 1.

Example 42

[0098] The same manner as Example 1 was performed, except that 5.0 parts
by weight (31% of the crosslinking compound) of the acrylate-based
compound was used instead of 0.8 parts by weight (5% of the crosslinking
compound) of the acrylate-based compound represented by Formula 6 in
Example 1.

Example 43

[0099] The same manner as Example 1 was performed, except that 0.5 parts
by weight (3% of the crosslinking compound) of the acrylate-based
compound represented by Formula 7 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 44

[0100] The same manner as Example 1 was performed, except that 5.0 parts
by weight (31% of the crosslinking compound) of the acrylate-based
compound represented by Formula 7 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 45

[0101] The same manner as Example 1 was performed, except that 0.5 parts
by weight (3% of the crosslinking compound) of the acrylate-based
compound represented by Formula 8 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 46

[0102] The same manner as Example 1 was performed, except that 5.0 parts
by weight (31% of the crosslinking compound) of the acrylate-based
compound represented by Formula 8 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 47

[0103] The same manner as Example 1 was performed, except that 0.5 parts
by weight (3% of the crosslinking compound) of the acrylate-based
compound represented by Formula 9 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 48

[0104] The same manner as Example 1 was performed, except that 5.0 parts
by weight (31% of the crosslinking compound) of the acrylate-based
compound represented by Formula 9 was used instead of 0.8 parts by weight
(5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 49

[0105] The same manner as Example 1 was performed, except that 0.5 parts
by weight (3% of the crosslinking compound) of the acrylate-based
compound represented by Formula 10 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 50

[0106] The same manner as Example 1 was performed, except that 5.0 parts
by weight (31% of the crosslinking compound) of the acrylate-based
compound represented by Formula 10 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 51

[0107] The same manner as Example 1 was performed, except that 0.5 parts
by weight (3% of the crosslinking compound) of the acrylate-based
compound represented by Formula 11 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 52

[0108] The same manner as Example 1 was performed, except that 5.0 parts
by weight (31% of the crosslinking compound) of the acrylate-based
compound represented by Formula 11 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 53

[0109] The same manner as Example 1 was performed, except that 0.5 parts
by weight (3% of the crosslinking compound) of the acrylate-based
compound represented by Formula 12 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 54

[0110] The same manner as Example 1 was performed, except that 5.0 parts
by weight (31% of the crosslinking compound) of the acrylate-based
compound represented by Formula 12 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 55

[0111] The same manner as Example 1 was performed, except that 0.5 parts
by weight (3% of the crosslinking compound) of the acrylate-based
compound represented by Formula 13 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Example 56

[0112] The same manner as Example 1 was performed, except that 5.0 parts
by weight (31% of the crosslinking compound) of the acrylate-based
compound represented by Formula 13 was used instead of 0.8 parts by
weight (5% of the crosslinking compound) of the acrylate-based compound
represented by Formula 6 in Example 1.

Comparative Example 1

[0113] The same manner as Example 1 was performed, except that 0.8 parts
by weight (5% of the crosslinking compound) of the acrylate-based
compound represented by Formula 6 was not used in Example 1.

Comparative Example 2

[0114] The same manner as Example 1 was performed, except that 8 parts by
weight of the binder BzMA/MAA (molar ratio: 70/30, Mw: 24,000) formed of
the alkali soluble resin was not used in Example 1.

Comparative Example 3

[0115] The same manner as Example 6 was performed, except that 8 parts by
weight of the binder BzMA/MAA (molar ratio: 70/30, Mw: 24,000) formed of
the alkali soluble resin was not used in Example 6.

Comparative Example 4

[0116] The same manner as Example 11 was performed, except that 8 parts by
weight of the binder BzMA/MAA (molar ratio: 70/30, Mw: 24,000) formed of
the alkali soluble resin was not used in Example 11.

Comparative Example 5

[0117] The same manner as Example 16 was performed, except that 8 parts by
weight of the binder BzMA/MAA (molar ratio: 70/30, Mw: 24,000) formed of
the alkali soluble resin was not used in Example 16.

Comparative Example 6

[0118] The same manner as Example 21 was performed, except that 8 parts by
weight of the binder BzMA/MAA (molar ratio: 70/30, Mw: 24,000) formed of
the alkali soluble resin was not used in Example 21.

Comparative Example 7

[0119] The same manner as Example 26 was performed, except that 8 parts by
weight of the binder BzMA/MAA (molar ratio: 70/30, Mw: 24,000) formed of
the alkali soluble resin was not used in Example 26.

Comparative Example 8

[0120] The same manner as Example 31 was performed, except that 8 parts by
weight of the binder BzMA/MAA (molar ratio: 70/30, Mw: 24,000) formed of
the alkali soluble resin was not used in Example 31.

Comparative Example 9

[0121] The same manner as Example 36 was performed, except that 8 parts by
weight of the binder BzMA/MAA (molar ratio: 70/30, Mw: 24,000) formed of
the alkali soluble resin was not used in Example 36.

Test Example 1

Test of Strength of the Thin Film and Developing Property

[0122] After the uniform thin film was formed by coating the
photosensitive compositions obtained in the Examples and Comparative
Examples by the method such as spin coating, slit coating, dip coating,
or doctor blading, the solvent was volatilized by performing the prebake
process at 100° C. for 200 sec. The thickness of the dried thin
film was about 4 microns. Next, the thin film was exposed under the high
voltage mercury lamp by using the photomask constituted by lines having
the interval width of 5 microns from 5 to 50 microns. The exposed
substrate was developed in the spray manner in the 0.04% KOH aqueous
solution at the temperature of 25° C., washed with pure water, and
dried by air blowing. Thereafter, the final thin film was formed by
performing treatment in the oven maintained at 210° C. for 30 min.

[0123] In order to confirm strength of the thin film, an experiment using
a press was performed. The strength of the thin film was measured by
using Nano-indenter and Berkovich Tip manufactured by MTS Co., Ltd.

[0124] In order to confirm a stripping characteristic of the thin film
obtained in the above experiment, the stripping solution in which KOH was
dissolved in a solution where benzyl alcohol, isopropyl alcohol, and
distilled water were mixed at a ratio of 1:39:60 so that the pH was about
14, was used.

[0125] After the thin film obtained in the above experiment was dipped in
the stripping solution maintained at about 60° C., the time until
the thin film was completely removed from glass was measured. The thin
film was sealed after being dipped therein in order to minimize a change
of the pH of the stripping solution.

[0126] The experimental results according to Examples 1 to 56 and
Comparative Example 1 are described in the following Table 1.

[0127] Comparative Example 1 as the standard experiment is the case where
no acrylate-based compound was used. When compared to this, in the case
of Examples 1 to 56, the stripping time was shortened according to the
content of the acrylate-based compound. This phenomenon is considered to
occur because the stripping solution is easily penetrated into the thin
film by a bulky characteristic of the adamantyl structure positioned at
the center of the acrylate-based compound. In addition, it can be seen
that the case where the addition amount is 25% or less and specifically
20% or less on the basis of the crosslinking agent does not largely
affect the strength of the thin film.

[0128] In order to confirm the viscosity of the photosensitive
compositions obtained in Examples and Comparative Examples, the
experiment using the capillary viscometer was performed. The viscosity
was measured by the ViscoClock manufactured by Schott Co., Ltd.

[0129] In addition, in order to confirm the patterning effect, after
developing was performed by using the compositions of the Examples and
Comparative Examples, whether the pattern was formed or not was observed
by using the scanning electron microscope.

[0130] The experimental results according to Examples 1 to 56 and
Comparative Examples 1 to 9 are described in the following Table 2.

[0131] Comparative Examples 2 to 9 as the standard experiment are the case
where the binder is not used. In the case where the binder was used,
since the viscosity was controlled to 11 to 20 cSt, the thin film could
be formed. However, in the case where the binder was not used, since the
viscosity was 2.5 cSt, it was difficult to control the viscosity and the
thin film could not be formed.

[0132] In addition, in the case where the binder was used, the patterning
was possible, but in the case where the binder was not used, the
patterning was impossible. After developing was performed by using the
composition of Example 1, whether the pattern was formed or not was
observed by the scanning electron microscope, and the results are
illustrated in FIG. 1. In addition, after developing was performed by
using the composition of Comparative Example 2, whether the pattern was
formed or not was observed by the scanning electron microscope, and the
results are illustrated in FIG. 2. FIG. 2 illustrates that it is
impossible to form the pattern. In the patterning test of the following
Table 2, O means that it is possible to implement the patterning, and X
means that it is impossible to implement the patterning.

[0133] As described above, since the acrylate-based compound according to
the exemplary embodiment of the present invention includes at least one
acrylate group with the adamantyl structure as the center, the compound
may be more usefully applied to the photosensitive composition. The
photosensitive composition according to the exemplary embodiment of the
present invention may shorten the developing time in the photolithography
process without decreasing strength of the thin film.